Welcome to Earning Abroad! In this series I’ll introduce you to some inspiring and ambitious friends I’ve met on the road — friends who have found viable work away from their home countries.

Heather Holt is yet another Earning Abroad interviewee who will seem very familiar to many of you. A fellow Yes Girl, she’s one of my favorite travel buddies thanks to our shared interests in scuba diving, petting stray dogs, partaking in boozy brunches, lugging our dSLRs around, and heavy doses of laptop time. It all started in The Cayman Islands in 2010, when I interned for Heather Holt Photography and trained with Heather in underwater videography — my first time diving with a camera in hand. Over time we transitioned to friends, and have found ourselves meeting up in exotic locations around the world on a regular basis. First we teaming up for our friends’ wedding in Philadelphia (perhaps not the most exotic), followed by epic adventures on Oahu and The Big Island, and most recently, an impromptu expedition to the Philippines. And this certainly isn’t the last you’ll be seeing of her — Heather is my partner-in-crime for my our upcoming sojourn to Tomorrowland!

An Illinois native, Heather has an amazing story. After years of hopping around the globe doing dive and photography work, she honed in on the Cayman Islands as the perfect place to launch her own business. Four years later and she’s absolutely killing it — and about to head across the world once to start from scratch once again. Over to Heather!

AB: Walk us through a typical day on the job.

HH: There are two types of days, shooting days and editing days, but I do some form of work every single day of the week and most of the time it is a combination of both.

On shooting days I typically have two shoots and I usually stagger them for morning and evening. On those days I wake up and do a portrait shoot on the beach or a real estate shoot in condos anywhere between 10am-1pm. It is pretty hot on the beach at that time but the water and sea pop with blues and turquoise so the photos are worth it in the end, as long as everyone is not squinting their eyes shut. And in the condos the light is stunning that time of day. I then grab lunch and head home to do emails, work on a blog post, edit shoots etc., before running off to a sunset shoot. After a long beach walk with my dog, working out and making dinner, then I get down to the real editing. I am a night owl and start work at about 10pm and work until about 4am!

On non-shooting days I mostly work from home doing computer work, blog posts, email, edits, as well as banking and errands. I try to give myself the weekends off from most work. Many times I will have a shoot but I try to enjoy spending time with my friends while they are off, so I lay off the heavy editing. However an email session at least once a day is a guarantee when you run your own business.

How long have you been a photographer?

I took my first photo class with Mr. Silvester when I was fourteen, a freshman in high school. I pretty much have not put my camera down since.

How did you come to run a photography business in the Cayman Islands? What inspired you to create this business?

I studied photography all through high school, and then went on to study photojournalism at Ohio University. Once I graduated I was OUT! I knew from my various study abroad programs and travels throughout my educational years that I wanted to make travel and living abroad a way of life, so with that college degree that my parents made me finish (best advice ever by the way) I moved down to the Cayman Islands to get my PADI Dive Instructor license and work as a beach/dive bum.

I guess I needed a break after my fairly intensive Photo Journalism education because I did not really pick up my SLR camera for about 2 years after college. I just enjoyed diving and got my first underwater photo/video experiences under my belt.

In 2004, Hurricane Ivan rocked the island and blew me off Grand Cayman and on to Thailand. That is when my passion for photography and my true style really emerged. I blended my high school fine art photography training with my university Photojournalism training and put my skills and eye into making artistic travel photos, which is my true passion. I ended up travelling all over Southeast Asia building my portfolio and working on various projects and publications, including a coffee table book on luxury eco resorts around the region. I also worked as a dive instructor and underwater photographer on Koh Phangan in Thailand and had a bit of a whirlwind of back and forth years back to Grand Cayman, then back to Thailand, and travelling and taking kick ass photos in between.

At some point I decided I should “TRY” to live in the states, be a grown up, do what a woman of her late 20’s should do and get a “real” job. So I moved to Venice Beach, became a Red Carpet photographer and went totally broke. I decided civilization the way most people know it was just not — and was never going to be — for me. I took advantage of my one-year lease to take a few classes to brush up my web/business skills, and peace-ed out back to Grand Cayman. In January of 2010 I launched Heather Holt Photography and have been working my ass off to make it successful ever since.

How did your family and friends react to your initial departure?

The initial departure from my family was almost the easiest. Of course I was young and had strong connections to “home,” but it was an adventure and my family was excited for me. Luckily they like to travel and have visited me everywhere I have decided to live. It was when the reality set in when I was not going to come “home” that the reaction of my family turned from positive to well… shall we say not quite as supportive as they started out.

As far as friends, living away from where you grew up and living all over the world you make a lot of them — you keep those special ones and the other ones fade away. It’s the special ones that will and do support you through all your hair-brained adventures. I have only a small few friends from where I grew up, but I have friends from everywhere I used to live/travel and friends that I Skype and meet up with all over the world.

How much money do you make? Is it enough to live on?

The amount of money I make varies month to month due to the cycles of the island’s high and low seasons. In a busy month I have made more than $10,000 — enough to cover salary, business expenses and put a big chunk in the bank for my personal savings. However that is not the norm and those busy months are essential for surviving the slow ones, where I have to cover business expenses which include my business license and work permit, gear maintenance and upgrades, web hosting and marketing materials. On the other side of the spectrum during those slow months I have made just enough to live and run a business on, around $3,000. Then there are the months I make nothing because I am off the island spending it all, ha!

But in all reality these slow tourist months are slow for everyone on the island and usually a really good time to go away to take a break and re-charge. It is hard to not get stressed with those slow months, however now that I have been doing this for four years I have faith that it will pick back up and I try to enjoy the lull and catch up on editing, blogging and personal projects. On average what I make is certainly enough to live on even on a very expensive island and allows me a great lifestyle.

What kind of legal hoops do you have to jump through?

Running a business in the Cayman Islands has many hoops to jump through, but it is possible. Every on-island business must be at least 60% Camanian owned, and as I am not Camanian, I have a business partner that technically owns 60% of my business and I the other 40%. Luckily my partner is a long-time friend and he gives me the independence to run the company as I please.

Once I had the partner we had to set up the company and get a Trade and Business License. When that was approved I needed a work permit. All foreign workers must have a work permit that is renewable every 1-2 years depending on the kind of permit that has been applied for and approved. Since all jobs must be offered to Camanians I had to advertise for my own job in the newspaper for two weeks straight. Luckily no one was qualified… or even applied… so I got the job! Once the initial set up was done, which was around CI$4,500 ($5,500USD), maintaining the business and permit is about CI$3,000 ($3,650USD) per year including my personal work permit.

What skills do you need for this job?

Because it is just me and my super-small business I literally do everything. I have to be on top of renewing all the governmental stuff, annual returns, work permits and trade and business. I have to be sure I am marketing and selling myself so business is actually coming in and I am making money. This means I have had to create my website, blog, and Facebook page and keep up with them all on a very regular basis. I try to post at least once a week. I have to respond to emails immediately as that has proven the best way to get that business locked down. Luckily I don’t really do my accounting as I am a math misfit, so I do my invoices and pass that onto my lovely mother to process and count.

Then of course there is the creative side. I have twenty years of photography experience and training, including underwater photography and video. Also, I have to edit the photos and design albums in a timely manner, which requires knowledge of the wonderful and life-giving Adobe programs.

What are the best and worst things about owning a photography business in the Cayman Islands?

Best thing by far is doing whatever the heck I want whenever I want to! I can schedule in my shoots to suit my schedule, which means I can sleep in (I hate early mornings!), go to social functions, beach walk my dog and go for runs, work from home in my pjs, meet friends for lunch and best of all take a few months off every year to travel. All that while staying busy doing shoots and editing from the comfort of my couch… or the beach. Best boss eva!

The worst thing is the boredom of Cayman. It is such a small island and I shoot in the same places all the time so inspiration is hard to come by. Plus, I would love to have someone around to chat to once in awhile during the day, run ideas by, ask about what to post, ask about designs, etc. It would be nice to have that work camaraderie and bonding that people get when they work in a community or office atmosphere.

What would your advice be to someone seeking to do the same?

Well it is a small and competitive industry here on the island and I would advise someone to not do it because you will be my competition! Haha, they can work for me instead. But seriously it is a very competitive market and my advice would be go somewhere where the industry is not quite as saturated with photographers. Having said that all of us established photographers, despite competing for the business, have enough bookings to make a good living on… a plus of doing business in a touristy place.

But in all reality it takes drive, talent and good photography skills, a bit of side income while you are trying to convince people to hire you as a photographer, and lots and lots of hard work and hours making it all happen. So be ready to work. When I first started I was happy to work for trade to just get my name out there. I did a few shoots for the radio station and in return I did a radio interview and they put a big advertisement on their website. I was also the primary photographer at the new yoga studio in return for free yoga. I also looked up all the charity events happening on the weekends and volunteered to shoot the event for free. This really helped to get my name and my work out there for people to start recognizing my brand. You put in hours you would never put in if you were working for someone else, but since it is for you, you put in even more. Now that I have worked for myself for so long I don’t think I could ever go back!

What do you know about the Cayman Islands that you wouldn’t have learned as a tourist? How did working in Cayman change your experience there?

Being a tourist here, or anywhere you are generally totally blind to what goes on behind the scenes, how the community feels and runs and the overall sense of daily life. “Oh this place is paradise you must love living here.” I get that a lot and yes living here has definite perks, but life is life and bills have to be paid, work has to get done, and rushing around and stressful days happen even down here in paradise.

Also being apart of the expat community here is amazing. I have learned so much about different countries and cultures. The diversity in the work force is huge for being such a small rock and I pride myself in having a very culturally diverse, as well as occupationally diverse group of friends.

Are there differences between working in your home country and in the Cayman Islands?

I have really only every worked part-time summer jobs in the US as a kid, so I have no idea what it is like working full time there but it looks hectic from what I see from friends and family. It seems there is LOTS of pressure and very little gain. Cayman is easy — no taxes, a strong currency, lots of holiday time (most people are free to take about 3-4 weeks), free time at the beach and underwater, and no boss (well for me at least!)

Have you had other experience working abroad?

As mentioned, I worked as a dive instructor and underwater photographer in Thailand. I looooooooved it. It was a very different experience working over there as most of the tourists were backpackers and in a similar life position as myself at the time. It was fun and I had a lot in common with my customers. Plus, Thailand is an amazing country and I looked forward to every meal!

What are your plans for the future?

I love Asia so much, I cherish the time I have spent there and I just keep being drawn back to it. So I am planning a six month trail move to Bali this winter. I will keep my business open here in Cayman with an employee doing my shoots, and take bookings for high season next year. During my trial I will try to tap into the HUGE destination wedding industry that is thriving in Bali.

If I can break into that and start a successful photo business there I would eventually hope to get some land, build a small B&B with a great community space, and do some sort of Art House Escape where people can come and stay and do workshops: painting, photography, yoga etc. in the exotic tropical jungle and beaches of Indonesia. This also going well, I hope to put a portion of the profits and activities of the B&B into animal rescue. This is the grand plan and who knows where exactly it will lead but I am well up for the challenge and the ride it takes me on, and if all else fails Grand Cayman is just not that bad of a place to call home at the end of the day.

Many thanks to Heather for sharing her story with us and let’s all wish her luck in her upcoming endeavor! And now that we’ve done a couple of these, is there a question you’d like me to be asking interviewees? Let me know in the comments.

You can find out more about Heather Holt Photography via her website, blog, or Facebook page. Though based in the Cayman Islands, Heather regularly travels around the Caribbean and the world for photoshoots.

Hi Guy, thanks for the comment. Having unsteady income is actually not bad at all since it always evens out and ends up at a pretty satisfactory level at the years end. Plus having the low season month (really only September) is great because I can go away on holiday and not worry about any loss of income! But I can see how it is not for everyone. I have been working in the tourist industry all my life so I am very used to the high and low seasons.

I shoot Nikon. I have a D300s, D7100, and D800. My favorite lens in 50mm f1.4. I never take it off my camera. I also shoot with 12-24mm f2.8. A great wide angle I usually use on my D800. I shoot with 2 cameras each with a different lens which allows me to be equipped for any situation.

I am a night owl and always have been. I would much rather sleep in than get up early, but with the loss of a morning means I must work another time. My natural body rhythm has always been to stay up late, I am just most productive then. The dog is sleeping and not antsy to go out, no one is wanting to chat, email or skype (with the exception of some friends on the other side of the world, it is a great time to catch them!) and finally the sun is not shining taunting me to come out and play.

Hi Heather/ thanks Alex for putting up this post.
Thank you for sharing how you have managed to make a living and work abroad, work for you. I think to understand the ebb and flow of the work is very important – wherever a person lives. Did you feel anxiety with living that way initially and if so, how did you deal with it? I’d love to know! 🙂

Hi Janice, nice to meet you! When I first started my business I was mainly making money working on the boats doing photo/video for Stingray City. Although it was not what I wanted to be doing long term, it was good reliable money coming in while I worked to get the top side work I was aiming for. It was very touch and go for the first year for sure and yes I was a bit worried now and again. I had tight strings on my wallet, lived very modestly and just worked my butt off! That was actually when Alex was interning for me and she helped me get much of my marketing going, and did some of the Stingray trips while I had meetings with event planners, condos or anyone else I thought would throw business my way. But all in all I had the drive to make it work and it did!

Hi Katie, I am just now getting familiar with the business structure in Bali, I think it is actually easier than here in Cayman, however as always there will be government fees and hoops to jump through. It will be an adventure to learn all about it!

The Red Carpet was totally surreal! I remember sitting there outside the Chinese Theatre and thinking to myself that a month ago I was at Sail Rock in Thailand photographing fish and now I am here. My head started to spin! I knew it wasn’t for me but it was a cool experience and great for the resume!

I loved this- so interesting to hear how you built up your business and make it work on the Cayman’s Heather. Your photos are absolutely stunning of course. I love your possible future plans for Bali- I second the ‘can I come to stay?’Comment above me. Sounds like my kind of place.

Thanks Nadia! Photography has definitely been a journey. When I was at Ohio University I got an absolute world class education from my professors. And yes I did Photo Journalism so that is what the main focus was. The whole topic of weddings and portraits, well, we mainly rolled our eyes at it. However in all reality that is where the money is and it is really not a bad gig. Especially on a tropical island where the beach is where everyone wants to be. Most of the people from my course I still keep in touch with do some form of photography still but many have veered away from the actual Photo Journalism path and are doing other forms of photography. Anyway thanks for passing on my story!

I love reading about others who are able to travel and/or live abroad and make a living doing something they love. I was actually pretty shocked about the income that is possible, even with the fluctuation. Heather is an incredible photographer for sure and definitely deserves the success!

Seconded 🙂 One thing to keep in mind too is the cost of living is very high in the Caymans (as everything must be imported) and as shown from the examples of the business set up fees and work permit fees, there are some high business expenses to handle as well. The salary Heather actually pays herself out of those amounts into her personal accounts is quite a bit lower than what the business grosses!

I used my Olympus XZ2 with an off camera strobe to take that angel shot. I would love to get a housing for one of my DSLRs… but I also like to travel. It was a tough choice to make but the housing for the XZ2 is small and compact and fits nicely in my carry on, yet it produces high quality images, even without the strobe.

This is a great series, Alex. I really like how honest Heather is. I get people telling me all of the time how lucky I am to live in paradise and how amazing it must be to be an expat … and it is … but, like Heather, there are still bills that need to be paid and work that needs to be done. Heather — you are really talented. Come over to SE Asia and teach me how to be a photographer!!

It looks like my husband will be taking work abroad, which means I will have to quit my current job as a flight attendant to follow him. I’m thinking of getting back into photography by starting my own business. How do you settle on a country to operate your business and how do check to see if there is a market for photographers?

If you contact the bigger hotels and tourism board they would be able to tell you if they do weddings, and how many etc. I also do lots of family portraits, which Americans love, so it would also be helpful to know the clientele. Starting a business in a foreign country can be quite complicated, many require a native business partner and there are usually lots of hoops to jump through that cost money. I have been living on and off Cayman for many years and knew the island well before I embarked on my photo business and I would definitely recommend living/visiting somewhere for more than just a 2 week holiday before making any investments and commitments. Best of luck to you!

Notify me of new postsSubscribe me to Alex in Wanderland's monthly newsletter

I'm a New York native who left my home to explore the world slowly and thoroughly. I’m just a little obsessed with photography, scuba diving, and reading guidebooks to countries I have no immediate plans to visit.